新型苯并噻吩稠合吡啶并[1,2-a]嘧啶衍生物的合成及其抑菌活性  

Synthesis and Fungicidal Activity of Novel Benzothiophene-Fused Pyrido[1,2-a]pyrimidine Derivatives

作　　者：徐姣 马玲[1] 刘秀波[2] 马伟[1,2] 马岩[3] 王道林[4] Xu Jiao;Ma Ling;Liu Xiubo;Ma Wei;Ma Yan;Wang Daolin(State Key Laboratory of Tree Genetics and Breeding,Northeast Forestry University,Harbin 150040;College of Pharmacy,Heilongjiang University of Chinese Medicine,Harbin 150040;School of business administration,Harbin University of Commerce,Harbin 150040;College of Chemistry and Chemical Engineering,Bohai University,Jinzhou 121003)

机构地区：[1]东北林业大学林木遗传育种国家重点实验室,哈尔滨150040 [2]黑龙江中医药大学药学院,哈尔滨150040 [3]哈尔滨商业大学工商管理学院,哈尔滨150040 [4]渤海大学化学化工学院,锦州121003

出　　处：《有机化学》2018年第7期1680-1686,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.31770688);国家公益性行业专项(No.201404718);哈尔滨市应用技术研究与开发资金(No.2017RAQXJ129);黑龙江省卫生计生委科研基金(No.2017-579)资助项目~~

摘　　要：利用Thorpe-Ziegler反应,通过2-氯甲基-4H-吡啶并[1,2-a]嘧啶-4-酮与2-巯基苯甲腈的环化制得2-(3-氨基苯并噻吩-2-基)-4H-吡啶并[1,2-a]嘧啶酮,继而在氨基磺酸作用下,通过Pictet-Spengler反应,设计合成了新型苯并噻吩并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶衍生物.初步抑菌活性试验表明,当浓度为50 mg/L时,化合物5b对黄瓜灰霉病菌和小麦赤霉病菌的抑制率达96%以上,5f对油菜菌核病菌的抑制率为98%,5g和5i对烟草赤星病菌的抑制率达93%以上.A series of novel benzothieno[3＇,2＇：2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidines are prepared via Pictet-Spengler reaction of 2-（3-aminobenzothiophene-2-yl）-4H-pyrido[1,2-a]pyrimidin-4-one using sulfamic acid as a catalyst, which in turn were obtained from the Thorpe-Ziegler isomerization of 2-（chloromethyl）-4H-pyrido[1,2-a]pyrimidin-4-one with 2-mercapto-benzonitrile. The structures of the products were characterized by FT-IR, ^1H NMR, ^13C NMR spectra and elemental analysis. The fungicidal activities of the prepared compounds were also preliminarily evaluated. For example, 5b exhibited more than 96% inhibition rate to Botrytis cinerea and Gibberella zeae at 50 mg/L, 5f exhibited 98% inhibition rate to Sclerotonia sclerotiorum at 50 mg/L, and 5g, 5i exhibited more than 93% inhibition rate to Alternaria alternata at 50 mg/L.

关 键 词：吡啶并[1 2-a]嘧啶 苯并噻吩 2-巯基苯甲腈 Pictet-Spengler反应 合成 抑菌活性 

分 类 号：O626[理学—有机化学] TQ450.1[理学—化学]